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The Wandering Path to a Dream Job

wandering path to dream job

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A popular quote these days is “Not all who wander are lost.” To me, this is strange because if you’re wandering, you can’t be lost. You have to have a destination in order to be lost and if you’re wandering, your destination is wherever you are. Why are we biased into thinking anyone who is wandering could be lost?

Instead, we could assume a person on a well-worn path doesn’t know where they’re going – that’s why they are following someone else’s footsteps. One time I followed a trail of litter and it was strenuous and terrible. Just because other people had clearly taken this path before didn’t mean that it was a good path. Meanwhile, when I made my own path on that trail- as I eventually had to do – I finally found what I was looking for.  And bonus, there was less litter.

Many of my friends took the well-worn pipeline of prestigious schooling to prestigious job. Now a decade later they are at a loss about where to go. Many paths are blocked so there is no clear path left. Other friends took meandering paths and are now hitting their strides. It make me wonder whether we are wrong about  assuming the direct paved path is the right one. The wandering path may lead you to a dream job, whereas the preset path may just lead you to nowhere.

What You Need for a Dream Job

Those who have reached their dream jobs realize that it’s different than what they expected. And those who didn’t reach their dream jobs may nonetheless have found success in a job nothing like their dream job. That’s why it can be a losing path to aim for that dream job. But that doesn’t mean that good and satisfying jobs don’t have things in common. Here are some tried and true things to look for, just so we know what we’re aiming at. We might not be aiming at a specific career but it doesn’t mean we don’t have things we are looking for.

You must provide value.

This seems obvious because what kind of employer wants an employee that doesn’t provide value? But it’s also true that if you’re not producing something of value, you will feel useless. I remember we had a year when my whole law firm was slow. It was the most miserable year of my career – even more miserable than when I quit. Even though I was getting paid the same salary to sit on my butt, it felt like I had no purpose and it made me anxious. You will be happiest in your job if you provide some value to the mission of the job regularly. You will be happiest when you are needed and growing.

Find areas where you can have autonomy.

The problem with law is that there is very little autonomy. The more money, the more senior your position – it doesn’t make it better. That’s true of many of our most valued jobs because we have such a hustle culture. But you want some independence, some mastery, some control.

Find good community and a place that fits your values.

Men often tell me that they would have been EXCELLENT lawyers. It would be so refreshing if they assumed they would be average attorneys, because that’s much more likely to be true.

It doesn’t mean that you can’t aspire to be the best, but the likelihood is that you’ll be average. You’ll have an average career, be average happy. If you find a career where the average person is happy, you’ll likely be happy too and, part of the reason for that, is you’ll be surrounded by generally happy people. Even if you’re a happy person, if you’re constantly surrounded by people who are unhappy, it’ll be hard to maintain your own happiness.

Look for something that is serving people.

People are happier when they’re helping others. This doesn’t mean that you should serve others at the expense of yourself. You should get paid and be treated well. But you have to connect what you’re doing to a greater purpose to really find it to be a calling.

Think about the worst parts of the job more often than the best.

People often tell me they would like to become lawyers because they love to argue but they don’t love documentation or deadlines. It reminds me of a story about a musician who attributed the length of his career to his love for practice and touring. He said the musicians who flamed out were interested in the fame and money.

Why the Direct Path to a Dream Job Might be a Loser

It’s not surprising that so many people hate their jobs. Currently, we make 18-year olds bet their life savings on 40-year careers. Further, we often judge educational success by the starting salary. So what could go wrong with basing your life’s work on a career with the highest starting salary at 22? So many things.

We don’t know how jobs will change.

If you had told people twenty years ago (or today) that people could make good money playing recording short dance videos on an app, they’d have thought you were daft. We didn’t even know how the jobs of today would change. People twenty years ago also would not have expected that white-collar workers would be regularly working 70 hours a week without a clear distinction between work and home life. This might be fine if you loved what your’e doing, but if you don’t, this can be too much to bear.

Many pre-prepared jobs are miserable.

Isn’t it weird how so many coveted jobs have obvious tradeoffs? We know investment bankers make a lot of money but we don’t think the job is fun or fulfilling. We know medical doctors go into a lot of debt, residency is grueling, and burnout is common. Most other people I know in white collar jobs work extremely long hours and aren’t particularly happy. And yet other people are putting in hundreds of hours and thousands of dollars to obtain one of these jobs. Maybe it makes sense to try something else when the path is difficult and the reward is middling.

Picking a pre-prepared career path means you are interchangeable.

The problem with many law jobs is that most lawyers have similar resumes. Many lawyers go into law school with little work history, then work at a firm, then try to escape by going in-house at a company. About 35,000 people graduate from law school each year and there are only 113,000 general counsel jobs total in the country. Further, when you have a general counsel position, you are likely staying there for awhile. So what I’ve seen is that my friend who is a partner in a law firm has applied to hundreds of general counsel positions without a bite.

The problem with setting a clear destination is that other people can set that clear destination too. Then you’re all chasing that same brass ring. You have direct competition for everything that you do and you realize that employers have no reason to see you as any different from the hundreds of other applicants.

You will love something more if it’s yours.

The Endowment Effect describes the odd truth that people tend to value that things that belong to them over things they don’t own. If you create a job that is tailored more to your skills, you will value it more. But most of the time people are just sorted into pre-prepared jobs. These aren’t jobs they created and they aren’t jobs created for them. People know they are interchangeable, which makes them dislike their jobs more. But if your job is unique, you might like it more because by being in that unique job, it makes you feel special. It makes it feel like you are valued for your uniqueness.

You don’t need to figure out your career end point right now.

This leaves the possibility of creating a job. If you take a meandering path, when you eventually apply for a job, you have a much more interesting resume with tons of unique experiences to weave  a rich story and plenty of disparate connections. Plus you’ll just have a much wider idea of what job you could have or what you could be, and that expansive sense of self if well worth the wandering.

So how does one go about wandering to a dream job?

There are actually rules to wandering! Or at least things to keep in mind as people try to pull you back to the beaten path.

Prepare for the pushback.

It’s really difficult to wander. There’s extreme social pressure to stay on the beaten path. What you need to realize is that the pushback now will save you some trouble in the future when you look back and wonder, why did I blindly follow everyone else? So no, you can’t tell your immigrant parents that this will be the key to even more riches and fame – because you have no idea. But you can promise your parents you won’t ask for money.

Don’t get sidetracked by the money.

The reason you have to get your money There’s a great quote by B.J. Novak of The Office fame:

Any time I’m telling myself, “But I’m making so much money,” That’s a warning sign that I’m doing the wrong thing.

As he says, “money can always be regenerated. Time and reputation cannot.” It’s something I think about often when the allure of money releases its siren call. Chasing money sounds like a good idea at first, but it can trap you into a life you don’t want, costing you much more in the end.

Allow yourself to be passionate.

A lot of people will say that it’s unnecessary to care about your work. And sure, nothing is necessary. You don’t have to love your spouse either but it would be a whole lot better if you loved your spouse and your work because if you loved your spouse and your work, where you spend the vast majority of your time, you’d probably love your life because that’s your whole life right there. So yeah you don’t have to love your life, but why wouldn’t you try?

We talk a lot about following one’s passion, and there are people pro and against that idea. But it really doesn’t make sense not to follow something interesting in your career path. It doesn’t mean that if you love movies, that you will or should be an actress – but maybe you’ll work in Hollywood in production, law, music, etc. If you’re going to be an administrative assistant, you can be an assistant in the location you want, the industry you like – so why not pick one you love? Maybe it’ll go somewhere and maybe it won’t. But there’s no point in not trying to get something awesome.

You can be in the right career and the wrong job.

Most people who hate their jobs, gripe about coworkers, bad bosses, company culture, working conditions, and pay. You can switch jobs and change nearly all of those things. So don’t confuse terrible jobs with a terrible career.

Of course, certain careers spell out certain types of jobs. If you work in hospitality, you’re going to have to work weekends. If you work in law, you’ll have to do a lot of reading. If you hate these basic things, then yeah, this is the wrong career. But be very expansive in your idea of a career before you quit it just because you have a bad job.

Pick jobs where you will learn.

You can’t know if you’re going to love a job. See above about the reasons you might hate this perfect job you interviewed for.

I once enrolled in the most advanced free piano course in my college. It was so boring, I left after one class. It’s not enough to get a gold star or lord it over your people. You will stagnate if you put your bar so low.


If you take a direct path, obviously you get there faster, but you choose that end point in the beginning before you have any idea where it’s like. We often pick endpoints that are difficult and mysterious and when we get there, we are disappointed.

It seems like I took a pretty well-worn path to law. But I don’t regret the stops I made along the way. After I graduated from college, I quit the job I had lined up to teach for a year in China. Then after 7 years of working at a firm, I quit to take a sabbatical. Neither of these instances have really panned out in terms of money, necessarily, but for me, it panned out because I have less regret. I took the chances when they came, and I found that a legal career was still waiting at the end of it. What I would like to encourage is flexibility in the journey. The things we think are ephemeral (a stable job) can be found later but the adventure, the passion, the possibility – sometimes we lose that if we wait too long.

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